Hi,
Wow, this is hard to live with. The tricky part of judging our past decisions in life is that now we know a bunch of things that we did not know then. Now, things appear crystal clear, but we must consider that they did not look like that to us then. It reminds me my past profession assisting children to learn very closely: you could see children attitude when they got an insight or consolidated a new concept: they went right to the bone. Before they were rambling around, trying, non sense errors, using multiple aids. Once they learned something, they discarded all those behaviors. If you asked them if they wanted some of old aids or procedures, they would tell you " what for", offended, as if they had never needed these tools in the past. They could call those tools as silly ones, or call silly themselves. It was themselves in the present judging themselves in the past.
I do not know your case, so what I am saying may not apply to you, but to me, judging myself in the past it is a temptation I have to avoid. When I participated in the church I was told it was almost like a sin of pride. They told me to put the past in God hands and to begin again. Sometimes, it works for me, even though I am not a believer right now. I was told that to be more spiritual, I needed to practice detachment, including detachment from what I did in the past (both, good and bad things). It is difficult, though, but it brings relief